The biggest problem I seem to have with headphones is that I just throw them anywhere in a hurry, and the wires get all tangled in stuff.
I am very, very careless with my headphones so over the past year, I've been through around 7 different pairs, which in total were probably ~$5/each as a mix of earbuds and headphones.
- Lose sound on one side - Glue dries away and plastic falls apart - They get tripped over (I have a very long wire running from my PC to my chair) - I usually throw them down because many cases I suddenly need to stop what I'm doing go and do something else.
Biggest issue is I don't buy thing online, and if I were to spend actual money (in comparison to $5, I would probably do it for Christmas or something).
So durability is key. I don't give a crap how they sound, and they're for my PC so they can be bulky.